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Search results; Over 1,000 homes in Windham

Apartment in Windham
Luxury 2BR | Wood Fireplace | Near Windham Mtn
2 bedrooms, 4 beds, 2 private bathrooms
13–18 Sept
,
4.74 out of 5 average rating, 27 reviews
Top guest favourite
Chalet in Windham
Stargazing Dome|Sauna|Firepit|HotTub|Pet Frndly
5 bedrooms, 9 beds, 4.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 99 reviews
Home in Windham
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds, 5.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in Windham
Aframe Escape | Hot tub | Movie Room | Karaoke
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 58 reviews
Chalet in Windham
Windham Peak Chalet
3 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
New place to stay
Top guest favourite
Chalet in Windham
Velvet Timber Haus | HotTub, Sauna, Firepit, Games
7 bedrooms, 11 beds, 3.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Chalet in Windham
Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm
5 bedrooms, 9 beds, 4.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 174 reviews
Guest favourite
Home in Windham
Pool |MTNView| HotTub |Sauna| Games|Movie| Firepit
6 bedrooms, 9 beds, 3 bathrooms
5–10 Oct
4.97 out of 5 average rating, 37 reviews
Guest favourite
Home in Hensonville
Spacious Townhome for an Upstate getaway!
2 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 13 reviews
Guest favourite
Cabin in Windham
Cozy Family-Friendly A-Frame - Windham with AC
4 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Chalet in Windham
Gorgeous Lodge | Mt View, HotTub, Firepit, Game Rm
4 bedrooms, 8 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 184 reviews
Guest favourite
Townhouse in Windham
Cheerful and Cozy 2 bedroom home in Windham
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Cabin in Windham
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 197 reviews
Top guest favourite
Apartment in Windham
Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub
4 bedrooms, 7 beds, 4 bathrooms
22–27 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Townhouse in Windham
Windham Mountain Village 2 bedroom townhouse
3 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
4.91 out of 5 average rating, 138 reviews
Top guest favourite
Home in Windham
Beautifully restored 6 BR in the heart of Windham
6 bedrooms, 10 beds, 3 bathrooms
18–23 Sept
4.98 out of 5 average rating, 57 reviews
Guest favourite
Townhouse in Windham
Mill House 2 | 3BD + 3.5 Bath Catskills Retreat
3 bedrooms, 5 beds, 3.5 bathrooms
14–19 Sept
4.92 out of 5 average rating, 78 reviews
Home in Windham
Cascade House Alpine Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
New place to stay
Top guest favourite
Home in Windham
Catskills Retreat with Theater, Hot Tub and Games
8 bedrooms, 14 beds, 3.5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 98 reviews